Digital streaming/library

Perhaps the best program you can use with Windows is free EAC (Exact Audio Copy).  This program will try to go over same unreadable sector more times than ITunes, that eventually will start interpolating or even dropping out samples - big advantage with scratched CDs, not so much with new.  Selecting format to use is another story.  ALAC, that I use, is more of an Apple thing, while FLAC is not supported by Itunes.  Best choice for you might be AIFF because it can hold metadata.  It takes more space than FLAC, but storage is cheap, these days.  Be sure to create backups.  

easola01, I would check first if you can hear any difference between formats.  In addition, many high res files are just 16/44.1 up-sampled.  They end-up with more bits and higher sample rate but don't carry more information.  My DAC up-samples data anyway.  I also have thousands of CDs that I keep on external hard drive in ALAC.  I Wi-Fi them to Airport Express that feeds Benchmark DAC3, using ITunes.  With this scheme I'm limited to 16/44.1 but don't have to worry about anything related to computer (speed, playback program, amount of memory, electrical noise etc) since my DAC always gets bit perfect 16/44.1 data.

Shadorne, I thought I checked it but it was long time ago.  I will check again.  Thank you.

easola01, It is best to avoid conversion by Audio Core.  Because I play 16/44.1 I set Audio Media to 16/44.1.  I tunes gets my CD without any conversion as 16/44.1 and sends it to Airport Express as a data.  Airport Express send it to my DAC as 16/44.1

Shadorne, Audio Media was set as 16/44.1    In fact AirPlay was not even shown as output device.  When I added it, it showed as 16/44.1

easola01, I'm not familiar with streaming.  My whole library consist only of CDs on HD  in ALAC format.

I rip data out of my CDs using (free) XLD for MAC.  I store ripped data in ALAC format, that is lossless compressed file.

AIFF is as good as FLAC but files take roughly twice more space.  ITunes doesn't play FLAC.